This invention relates to novel sulfonylurea herbicidal compounds, agriculturally suitable compositions thereof and a method of using them to control the growth of undesired vegetation.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years. A multitude of structural variations exist within this class of herbicides, but they generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings.
U.S. Pat. No. 4,394,506 discloses herbicidal orthoalkoxycarbonylbenzenesulfonamides such as ##STR1## wherein wherein
R.sub.2 is H, F, Cl, Br, C.sub.1 -C.sub.3 alkyl, NO.sub.2, SO.sub.2 CH.sub.3, OCH.sub.3, SCH.sub.3, CF.sub.3, N(CH.sub.3).sub.2, NH.sub.2 or CN;
X is H, Cl, CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3 or OCH.sub.2 CH.sub.2 OCH.sub.3 ; and
Y is H, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 substituted alkyl, C.sub.1 -C.sub.4 alkoxy, alkylamino, dialkylamino, etc.
South African Patent Application No. 81/4874 discloses herbicidal sulfonamides of formula ##STR2## wherein
A is a C.sub.1 -C.sub.6 alkyl radical which is substituted by halogen or various other organic substituents or a C.sub.2 -C.sub.6 alkenyl radical which is substituted or unsubstituted.
X is O, S, SO or SO.sub.2 ;
R.sub.1 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or YR.sub.5 ;
R.sub.2 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkyl, CO.sub.2 R.sub.6, YR.sub.5, NO.sub.2 or CONR.sub.7 R.sub.8 ; and
R.sub.3 and R.sub.4, each independently of the other, are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, halogen or alkoxyalkyl of at most 4 carbon atoms.
South African Patent Application No. 82/5042 discloses herbicidal sulfonamides of formula ##STR3## wherein
A is C.sub.3 -C.sub.6 alkynyl;
X is O, S, SO or SO.sub.2 ;
R.sub.1 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or YR.sub.5 ;
R.sub.2 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkyl, CO.sub.2 R.sub.6, YR.sub.5, NO.sub.2 or CONR.sub.7 R.sub.8 ; and
R.sub.3 and R.sub.4, independently of one another, are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, halogen or alkoxyalkyl of at most 4 carbon atoms.
South African Patent Application No. 82/5671 discloses herbicidal sulfonamides of formula ##STR4## wherein
A is a C.sub.1 -C.sub.6 alkyl radical or a C.sub.2 -C.sub.6 alkenyl radical which is substituted by halogen or various other organic substituents;
X is O, S, SO or SO.sub.2 ;
R.sub.1 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or YR.sub.5 ;
R.sub.2 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkyl, CO.sub.2 R.sub.6, YR.sub.5, NO.sub.2 or CONR.sub.7 R.sub.8 ;
R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, halogen or alkoxyalkyl of at most 4 carbon atoms; and
R.sub.4 is C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkylthio.
South African Patent Application No. 82/7439 discloses herbicidal sulfonamides of formula ##STR5## wherein
A is a C.sub.3 -C.sub.6 alkynyl group, a C.sub.1 -C.sub.6 alkyl group which is substituted by halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 haloalkylsulfinyl or C.sub.1 -C.sub.4 haloalkylsulfonyl, or it is a C.sub.2 -C.sub.6 alkenyl group substituted by one of the above substituents;
X is O, S, SO or SO.sub.2 ;
R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or a YR.sub.6 group;
R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkyl, YR.sub.6, CO.sub.2 R.sub.7, NO.sub.2 or CONR.sub.8 R.sub.9 ;
R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, halogen or alkoxyalkyl having at most 4 carbon atoms;
R.sub.4 is hydrogen, methyl or ethyl;
R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, methoxymethyl, cyanomethyl or cyanoethyl;
R.sub.6 and R.sub.7 are each C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or C.sub.2 -C.sub.6 alkynyl;
South African Patent Application No. 83/0441 (Swiss priority 1/25/82) discloses herbicidal benzenesulfonamides of formula ##STR6## wherein
R.sub.1 is H, halogen, NO.sub.2, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.5 alkenyl or C.sub.1 -C.sub.4 alkoxycarbonyl;
R.sub.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms;
R.sub.3 is halogen, H, NR.sub.4 R.sub.5, C.sub.1 -C.sub.3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C.sub.1 -C.sub.4 alkoxy, or is C.sub.1 -C.sub.3 alkoxy, unsubstituted or substitutued by methoxy, ethoxy, or 1 to 3 halogen atoms;
A is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkenylene, each unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl;
m is 0 or 1;
E is N or CH;
X is oxygen, sulfur, SO or SO.sub.2 ; and
Q is, in part, OH, CN, NR.sub.6 R.sub.7, SO.sub.2 R.sub.8, cycloalkyl or COC.sub.1 -C.sub.6 alkyl.
South African Patent Application No. 83/3779 (Swiss priority 5/26/82) discloses herbicidal benzenesulfonamides of formula ##STR7## wherein
A is C.tbd.CR;
m is 1 or 2;
E is CH or N;
Z is oxygen or sulfur,
R is, in part, H, C.sub.1 -C.sub.9 alkyl or C.sub.1 -C.sub.9 haloalkyl; R.sub.1 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or YR.sub.5 ;
R.sub.2 is H, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 haloalkyl, YR.sub.5, CO.sub.2 R.sub.6, NO.sub.2 or CONR.sub.7 R.sub.8 ; R.sub.3 and R.sub.4, each independently of the other, are H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1-C.sub.4 haloalkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, NR.sub.9 R.sub.10 or OCH.sub.2 CH.sub.2 NR.sub.9 R.sub.10.
South African Patent Application No. 83/6449 (Swiss priority 9/1/82) discloses herbicidal benzenesulfonamides of formula ##STR8## wherein
R.sub.1 is H, halogen, NO.sub.2, amino, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.4 haloalkyl or a QR.sub.7, CO.sub.2 R.sub.8 or (CO).sub.n NR.sub.9 R.sub.10 radical;
R.sub.2 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, halogen or alkoxyalkyl containing not more than 4 carbon atoms;
R.sub.3 is C.sub.2 -C.sub.10 alkenyl which is substituted by one or more fluorine or bromine atoms or by one or more hydroxyl, cyano, nitro, (Y).sub.m CO(Z).sub.n R.sub.8, SO.sub.2 NR.sub.11 R.sub.12, S(O).sub.p C.sub.1 -C.sub.3 haloalkyl or S(O).sub.n C.sub.1 -C.sub.3 alkyl groups and which may additionally be substituted by one or more chlorine atoms;
R.sub.4 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy;
R.sub.5 is H, halogen, NR.sub.13 R.sub.14, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.2 haloalkoxy; and
E is CH or N.
South African Patent Application No. 84/2245 (Swiss priority 3/28/83) discloses herbicidal sulfonamides of formula ##STR9## wherein
A is C.sub.1 -C.sub.6 haloalkyl;
R.sub.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, COR.sub.6, NR.sub.7 R.sub.8, CONR.sub.9 R.sub.10 or SO.sub.2 NR.sub.11 R.sub.12 ;
R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl; and
R.sub.3 and R.sub.4, independently of one another, are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.1 -C.sub.4 alkoxy or NR.sub.12 R.sub.13.
South African Patent Application No. 84/2722 (Swiss priority 4/13/83) discloses herbicidal benzenesulfonamides of formula ##STR10## wherein
A is a radical of the formula CR.sub.6 R.sub.7 XR.sub.8, CR.sub.9 R.sub.10 R.sub.11 or CHR.sub.7 SCQR.sub.21 ;
R.sub.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, YR.sub.14, CONR.sub.12 R.sub.13, NR.sub.12 R.sub.13, SONR.sub.15 R.sub.16, OSO.sub.2 R.sub.17 or COR.sub.18 ;
R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl;
R.sub.3 and R.sub.4, independently of one another, are each hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.5 alkoxyalkyl or NR.sub.19 R.sub.20 ;
R.sub.9 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl;
R.sub.10 is hydrogen, halogen or methyl;
R.sub.11 is a radical COR.sub.24 or a C.sub.1 -C.sub.4 alkyl group that is mono- or polysubstituted by substituents selected from the group: cyano, nitro, hydroxyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, etc.
R.sub.18 is H, C.sub.1 -C.sub.4 alkoxy and various other organic radicals.
There is a continuing need for new herbicidal compounds which have safety to selective crops and which control both grassy and broadleaf weeds.